1400: The Duke of Rothesay bigamously marries Mary Douglas. The father of his spurned first wife gains support from Henry IV of England and an English army easily takes Edinburgh, except for the castle, before withdrawing.
1401: David Stewart, 1st Duke of Rothesay is captured by his uncle Robert, Duke of Albany and imprisoned in St Andrews Castle. He is subsequently moved to the Duke of Albany's home at Falkland Palace in Fife.
March 1402: David Stewart, 1st Duke of Rothesay dies at Falkland Palace as a result, the General Council decides, of "Divine Providence". Others say the cause is starvation. This leaves David's 7 year-old brother James as heir to the throne still held by Robert III. There are fears that James in turn will not be safe from the ambitions of his uncle Robert.
22 March 1406: James is captured by pirates off Flamborough Head in Yorkshire while en route to sanctuary in France. They then hand him over to Henry IV of England.
1407: The Duke of Albany negotiates a renewal of the long standing treaty of mutual support against England with France.
24 July 1411: At the Battle of Harlaw, 20 miles north of Aberdeen, the highland army of Donald of Islay, Lord of the Isles meets the lowland army of Alexander, Earl of Mar, son of the Wolf of Badenoch. At stake is the Earldom of Ross and control of northern Scotland. After an inconclusive day of heavy fighting and heavy casualties, Donald retires to Inverness and Alexander to Aberdeen.
1413: The University of St Andrews is founded as a center for learning and the arts.
1420: Robert, Duke of Albany dies and is succeeded as Governor of Scotland by his son, Murdoch.
December 1423: The Treaty of London provides for the release of King James I by Henry VI of England in return for a King's ransom of £40,000, plus £4,000 for the expenses incurred during James' 18 years of captivity.
April 1425: James I arrests many members of the Albany family, descendents of his uncle, Robert. James Albany evades long enough to attack Dumbarton and destroy the castle, so justifying a charge of treason against the family.
May 1425: The Scottish Parliament meets in Stirling to try the Albany family for treason. Murdoch and three others are executed and the family is virtually extinguished.
1428: James I summons Alexander, Lord of the Isles and other highland clan chiefs to a meeting in Inverness, and has them arrested. Three are executed as an example, but others including Alexander are later released.
August 1436: James I loses considerably credibility after his efforts to besiege the English in Roxburgh Castle fail miserably.
21 February 1437: James I is assassinated while staying at the Abbey of Black Friars in Perth. Queen Joan is injured but escapes with her son James. She arranged for the conspirators, including relatives of James I' to be caught and executed.
24 November 1440: The Livingston and Crichton families seek to secure their joint influence over the young James II by killing the Earl of Douglas and his brother in the presence of the King at Edinburgh Castle.